Transgression spoken of here is certainly what Daniel had prayed about in verse eleven: “Yes all Israel has transgressed Your law, and has departed so as not to obey Your voice…” Therefore, Israel’s transgression was a blatant disobedience to God, which is rebellion against God and a rejection of His laws and teachings.

But the definite article attached to the word in verse 24—the transgression—suggests that there is a more specific transgression that Israel as a nation is guilty of. We don’t see the definite article in verse eleven, I suppose because Daniel is not aware of any specific sin, but is focused more on the enormity of their disobedience. Gabriel’s prophecy, however, is specific and it is apparent to us now in this New Testament age that the transgression spoken of here is their total rejection of their Messiah. In John’s words, “He came to His own, and those who were His own did not receive Him” (Jn. 1:11).

The verb “to finish” simply tells us that Israel’s long trend of disobedience, and in particular their sin of rejection of their Messiah, will come to an end. But it will take a long time for this to happen. The whole nation of Israel has for a long time been under the spell of Satan to cause them to believe a lie and to not believe the truth about who Jesus is; so it will take a miracle for them to repent—a great revival.

I heard someone say recently, “You can’t help someone until they hit rock bottom.” I think this is what God has in mind for Israel. He will break them during the Tribulation. All during those seven years He will be chipping away at their hard heart, revealing to them their sin.

I believe their conversion (what is left of them) will be right at the end when they see Jesus; and they will all morn because of their sin of rejection of Him (Matt. 24:30). At this point, when their eyes lock, God will immediately pour on them “the Spirit of grace and of supplication” spoken of in Zechariah 12:10. This is none other than the Holy Spirit. Says MacArthur in his notes, “The Holy Spirit is so identified because He brings saving grace and because that grace produces sorrow that will result in repentant prayer to God for forgiveness (Matt. 5:4; Heb. 10:29).” So, at that point, they—as a nation, as every family by itself, and as every person individually—will confess their sins and ask forgiveness; thus all Israel will be saved (Zech. 12:10-14; Rom. 11:26-27).